Shipping Options

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This is potentially a bit of a complicated one, I don't really know where to start but would like at least a rough idea of what to do before speaking with Shopify Experts.

On my shipping options I have several options, Royal Mail, DHL Delivered to Door, DHL Delivered to Service Point and DHL Delivered to Depot. When selecting either the Service Point or Depot option I would like to add in a drop-down menu, preferably split into counties on the options they can choose from and get them to pick one before payment is made. 

Any ideas on how to do this or where to start?

Thanks in advance.